


Perverted Sentimentality

by Lemonjello



Category: Undertale (Video Game)
Genre: Alternate Universe - 1920s, Alternate Universe - Dark, Alternate Universe - Mobtale (Undertale), Alternate Universe - Underfell (Undertale), Dark Chara, Dark Frisk, F/M, Frans - Freeform, Genocide Route Frisk (Undertale), Grumpy Papyrus, Mafia Gaster, Mafia Papyrus - Freeform, Mafia Sans (Undertale), Slow Burn, Underboss Sans, Underfell W. D. Gaster, Undertale Genocide Route, mafiatale, roaring 20's
Language: English
Status: In-Progress
Published: 2019-04-06
Updated: 2019-04-18
Packaged: 2020-01-05 20:05:41
Rating: Not Rated
Warnings: Graphic Depictions Of Violence
Chapters: 5
Words: 15,423
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18373142
Author URL: https://archiveofourown.org/users/Lemonjello/pseuds/Lemonjello
Summary: "You lied to me. You've been lyin' to me this entire time. How can I believe a single thing that comes out of your filthy, depraved mouth? Did you ever feel anythin' for me at all? Are you even capable?""Life is one big joke to you. Why am I supposed to take you seriously when you cannot even do the same?"A 1920's Mobtale AU where Sans sees Frisk and he can't stop thinking about her





	1. Class Act Weiner

**Author's Note:**

> Hi guys! This is my first undertale fanfiction so let me know what you think! I love anything mobster au so I thought I would do the same with our favorite skeletons. I don't know who created this tag but all credit to you, ya masterpiece ~

The sight couldn’t have been stranger. Frisk always, _always_ made sure that she left the bookstore during her lunch at breakneck speed to ensure her quota for her biweekly hotdog. Not only was it her favorite stand for a multitude of reasons, but it was also the most popular one in town. Now, she loved a good old-fashioned dog as much as the next person, but these hotdogs are what one would consider _gourmet._ She was surprised they managed to sell them as cheap as they did. Unlike most hotdogs, these were 100% all natural American pork. No intestines, skins, snouts, or other rubbish added. Surprisingly enough, they were the only place that Frisk had seen to advertise this fact, and every other hotdog had seemed rather shady since. Other people seemed to think so too, which is why the line was bound to have you waiting ten minutes at least. Not so bad, but with the way they flipped the dogs into their freshly made glossy rolls (not buns – rolls) at a mile a minute, the wait was accompanied by a rather boisterous and agitated line full of customers. Frisk didn’t mind this, it was simply another reason why she loved this stand so much. Listening in on the gossip between construction workers, businessmen, and flapper girls, she was always sure to gain juicy little tidbits of much needed information.

 Not today. Today the line was close to nonexistent, save for one large patron at the front already in the process of paying the vendor.

 _Hm,_ Frisk mused, _maybe everyone found out that there’s snouts in it after all._

Chuckling to herself, she sauntered up to the line, not before noticing the real reason behind the stand’s sudden decline in business. She always prided herself on being an insightful gal, it was a bit of a gift really. Her twin brother had some of the same talents, but he was too unrestrained to remain the quiet and calculating type. Always preferred to get his information by chatting up the crowd. She couldn’t help but feel the corners of her mouth twitch up in a bemused smile. What she assumed to be the rest of the regulars were milling about the stand, doing their best to look disinterested and busy with other things. Many were having pseudo conversations with each other, and some had abandoned the stand altogether and were walking away in different directions. She would have concluded that the stand was finished operating for the day, if it hadn’t been the elegant stack of dogs with fresh grill marks filling up the water steamer.

The monster (it had to be a monster, it was at least seven feet tall!) in line was wearing a suit, and Frisk guessed that it had cost a pretty penny. The city had never tried its best to accommodate monsters, and their proportions were a bit difficult to tailor. This resulted in already expensive materials costing the monsters even more. Most elected to have their garb shipped in from New Hotland, where clothing was mass produced specifically for monsters and thus sold at better deals. She would have to see him turned around if she was going to judge his tastes. If it was a female monster, she would be surprised. No females in this town had any power or respect, monster or human, especially not enough to scare grown men away from their food. The closest thing they had was Toriel, and ever since the scandal that her husband Asgore had been involved in, the public opinion of her began to decrease exponentially. The thought brought a bit of suppressed rage bubbling to Frisk’s surface, but she kept her neutral expression. She preferred to save her emotions for when she had use of them.

No, this monster, this male monster, had provoked a response in Anri’s customers, and you would expect him to not look very happy about it. However, there was nothing but cool respect written in his posture, even if his eyes held fear in them. Perhaps the sweat dripping passed his bushy eyebrows was from nervous caution and not the steam? It didn’t matter. This was going to be the fastest Frisk had ever gotten her hotdog, even if she was going to have to feign ignorance to the present situation to get it. Besides, even if it really was some type of mobster before her, it’s not like it could be the monster Don. He wouldn’t be caught dusted eating at a hotdog stand. His lavish tastes were legendary. She doubted this monster was even from the administration, but you could never be too sure. There were no signs of a struggle or distress, no blood stained on the ashen pavement: he had most likely demanded to be in the front of the line or everyone had cleared just at the sight of him. Even a hungry, agitated mobster monster couldn’t be too terribly upset by having someone in line _behind_ them could they? And it wasn’t a safety concern for his well-being: Frisk was sure he could tear anyone else that was her size to pieces. The thought of any complaint on his part also sent rage into Frisk, an imaginary argument already taking place in her head.

_Can’t ya read a room lady? Line’s closed._

_That’s interestin, it sure had the appearance of being open to me. Step aside, you’ve been served already._

_What the fuck did you just say to me?_

_You heard what I said, buster brown, now SCOOT._

Of course this would never happen. Frisk would never be so foolish, but it was always fun to imagine. It stopped her from going crazy throughout the day. The big guy in line finished paying, and almost ran into Frisk in his hurry to leave. In his surprise, he dropped nearly a dozen ketchup packets to the ground, and Frisk noticed there were even more in his fist. His bony, pale fist.

 _Huh, I was wrong,_ Frisk thought nervously. _He is in the admin…_

From the response people were giving him and the obviously skeletal appearance, he had to be a Gaster.

_But to find out which one…_

She allowed herself to erupt into what she had discovered men to find a “charming” giggle, and she knelt down to process what she had just discovered. One knee on the pavement, she quickly swiped up the packets and stood just as swiftly.

_What the hell's a Gaster doin' at a hotdog stand? During the daytime? Out in public? These skelemonsters must be pretty powerful to wander around alone in a city full of racist humans._

“Looks like ya dropped something mister. It sure seems like you love ketchup!” She gave him her best timid smile. She couldn’t help but feel her pulse quicken as the surprise in his eye sockets switched to something colder. Each eye socket had a tiny pin prick of light in it, and his neutral expression contained a set of fanged teeth. One was capped in gold, and his lack of lips gave him a sinister appearance without trying. The suit was double-breasted, and the shoulders were soft and unstructured. In the jacket pocket, a blood-red handkerchief sat neatly folded, with the initials S.G. embroidered in black. Each gold button on the front of the suit had a molten G on them as well. His sleek black shoes looked like they had been freshly shined. Frisk stood at two feet shorter, and she had to crane her neck to try and meet his gaze.

“I musta been standin too close, huh?” she asked. This pulled him out of his quiet calculation, and he shook his head.

“not your fault, little lady,” he answered smoothly.

  _Jesus! That voice is richer than dark chocolate cake with a mortgage!_

He had said it at normal speaking volume, but Frisk could see how that voice could boom when he needed it to. It had a hint of gravel to it, and it was octaves lower than any man she’d ever heard. This was none other than Sans Gaster, the underboss to Don Gaster, and he was a violent, teleporting, bone wielding marauder. Frisk could hardly believe it. At _her_ hotdog stand?

 _Sound nervous, Frisky. A little scared and a little shy._ “A-anyways, here’s that ketchup,” she said. She averted her eyes, as if embarrassed for staring. She looked back up from under her lashes.

“do ya come here often?”

His question surprised her. She had hoped to gain information from this exchange, even if it was just from Anri. This lunch break was going to be eaten up if she didn’t get a move on. Before she answered, she walked up to the stand and quickly asked for the usual with a wink.

“I guess you could say that. It’s the best place in the city, I make sure I get one a few times a week on my work break.”

“ah, a gal afta my own heart,” he said with a smirk. “maybe it explains why you look _dog_ tired.”

Ah, something she had nearly forgotten about Sans. Aside from the bloodthirsty rampages he was known to go on, there were also the insufferable jokes.

“Aw, do I really? I guess it’s okay to mention that you look _bone_ tired yourself.”

His eyes (sockets?) widened, and for a moment she wondered if it was not appropriate to joke back. She felt herself growing uncomfortable under his gaze. It didn’t last long because with a short huff he replied “While I _relish_ this conversation, dollface, and I’d love to take some time to _ketchup_ with a dame like yerself, I really must be getting back to business. Let me treat ya though.”

He handed a neat stack of bills to Anri, and small red card to Frisk.

“hotdog _buns_ aside, I’d love to continue this some other time.”

Frisk allowed her mouth to form a small “o” in surprise, before quickly tucking the card into her dress pocket. When she looked up, the skeleton was already sauntering away. She thought about running after him to ask him for his name, but she remembered seeing lettering on the card he handed her. _Must be on there, along with some phone number,_ she thought. It would have seemed suspicious of her anyways, running after someone so elite and dangerous. She didn't realize she had been holding her breath until now. A dull throb began in her temples.

She didn’t have to wait in line at the vendor, had her meal paid for, and even had a telephone number for the infamous underboss Sans Gaster without having to snoop for it.

She couldn’t have had a luckier day.  


	2. Big Fish

**Notes for the Chapter:**

> Another short chapter. I'm trying to crank short chapters out frequently rather than long ones once a week :P

_damn, if I hadn’t stopped by that stand earlier I don’t think I woulda made it,_ Sans thought tiredly. The way his uncle and Paps were running him, you would’ve thought they mistook him for a water faucet. He knew he had a very special skillset, but even blessings like him needed a break! Just as he was about to collapse on the couch in a heap, Papyrus’s shrill voice made him freeze.

“NOT SO FAST BROTHER! WHAT DO YOU THINK YOU’RE DOING?” he asked, a reproachful frown on his face.

“I think I’m aboutta take a load off? I been breaking my backbone all day long getting those materials Gaster needs. Did you know how many different towns I had to go to? My magic is all but done for,” he snapped in annoyance. Papyrus had the good grace to soften his scowl a bit.

“I THINK A HOT SHOWER WOULD MAKE YOU FEEL MUCH BETTER, AND IT ALSO WOULDN’T GET ANY GRIME ON THE UPHOLSTERY I JUST HAND WASHED EITHER.”

Sans wanted to make a purposefully bad joke or sit on the couch just to spite him, but he was almost incapable of trying to hurt Paps’s feelings (and telling bad jokes). Almost.

“Alright alright, just please tell me you were too tired to cook and I can go get us all take out?” Sans asked.

“DO NOT WORRY SANS! DESPITE BEING EXHAUSTED AS WELL, I, THE GREAT PAPYRUS, HAVE STILL MANAGED TO PREPARE A MEAL FOR THE FAMILY! GO GET SHOWERED SO WE MAY ENJOY OUR TIME TOGETHER AND EAT MY CUISINE!”

Sans turned quickly to hide his disappointed expression. He was going to have to hit up that hotdog stand more often, if only to see the delightful little broad he’d almost bumped into earlier.

_Such a teeny tiny thing,_ he mused. He wondered if she’d called while he was out, but he seriously doubted it. His name was right there on the card. The only women that actively sought mobsters out were for money, or they were spies. Not to mention that humans did not think very highly of monsters. He had never given a human girl his phone number before, and for good reason. They were snotty, rude creatures. He couldn’t remember a time when one hadn’t glanced at him in horror, her lips curling back and her body stiffening. This dame was bolder than the rest, she even picked up his ketchup for him. Nearly jumped out of her skin when she saw his face, too. To her credit, when she spoke to him her voice didn’t even quaver. His mind wandered to her hunched over form, the dresses skirts gathering around her knees. Her hair had grazed the pavement, the golden curls floating in the breeze. _And those damn eyes… little fiery ambers…_ Even if she didn’t call, he’d be seeing her again. She said she went to that stand a few times a week during her break. She’d be easy enough to track down. Then he’d ask her why she never called and he’d see the little lady stammer for him. He let a deep chuckle rumble out. He was looking forward to it.

“SANS!”

_Oh, shit. What did I do this time?_ He really couldn’t think of it. Even though he liked his free time, business was business and he always took care of it when given the order. After his shower, he had started drying off, but was unable to even fully dress before his Uncle’s menacing voice boomed up the staircase. _Shit, shit, shit!_

W.D. Gaster wasn’t all bad. He was cold, calculating, and looked like the stuff of nightmares, but even he was known to show mercy on a few occasions. Like Gaster always said, _“let the punishment fit the crime.”_ That didn’t mean Sans wasn’t about to get his ass beat for screwing something up, though. He never begged to his uncle, and he never would. If he wanted a fight, Sans was sure to give him one, to an extent. He still always followed orders, and was always back on garbage business after healing up. _That’s the way family works_ , he supposed. _You can love em or hate em or both, but you_ _still gotta fuck with em._

“I’m comin! be there in a sec!” Sans shouted hurriedly. He already had to eat whatever variation of pasta Paps had cooked up, he didn’t want to be forcing it down a sore jawbone.

The house was eerily silent. Sans finished dressing as swiftly as possible, but the trepidation in him began to grow. Had he gotten blood on the downstairs carpet when he walked in? Did he forget one of the materials on his uncle’s list, causing a delay in plans? Was his bar tab too wracked up and Grillby was getting _heated?_ He let out a snort. _Bad Sans, this is no laughing matter._

Creeping down the staircase, he peered around the railing to see the back of his Uncle’s head. A jagged crack ran down it, two fractured pieces of skull overlapping like it had been attempted to be put back together. He was sitting in the recliner, casually puffing on a cigar. The thick grey smoke curled towards the open window and passed the trees in the fenced in yard. If anyone attempted to climb it, they would be promptly electrocuted and the bodies would fall through the trap doors surrounding it. A bit gruesome, but with Don Gaster’s love for fresh air, it was necessary for how often the windows were open. Couldn’t have anyone listening in on family business, not even the crew.

“ya wanted to see me?” Sans asked carefully.

“Yes, come sit down my boy,” Gaster wheezed softly, his voice taking on an eerie tone. Whenever he spoke, there was a soft reverb behind it, almost as if his words were being delayed and coming back to haunt everyone that heard him. Sans got comfortable on the couch, doing his best to look relaxed. After another long drag of his cigar, Gaster crushed the tip in a glass ashtray, resting the unfinished candela on the holder. He released the smoke slowly, allowing it to mingle with his magic and drip green plumes from his eye socket. He steepled his fingers, appearing to be deep in thought. Papyrus was nowhere to be seen. Whether he had been banished to his room or sent outside completely was a mystery. Sans decided not to comment on it.

“Sans, you’ve heard of the Misericordia’s, I presume?”

He wasn’t sure why the question stupefied him, but he recovered quickly.

“yeah, a’course I have. ain’t they that mafia that says they ain’t a mafia?”

Gaster considered this. “They do not confirm or deny that fact. They prefer the term ‘organization’. Discretion to their business is key. So much so in fact, that Don Misericordia has never been seen in public. Or by anyone outside of their group, for that matter.”

Sans was aware of this. Hell, everyone was. It was a well-known fact that the influence of the Misericordia’s stretched far and wide. Outlandishly wealthy for God knows what, the mobsters that belonged to the group had never flexed their power on innocent people. Sans respected that. Despite them being a rival mob in the same city, neither groups had encroached upon the other’s territory. He wondered if Gaster was planning on changing that.

“I’ve gotten quite a business proposition from one of their capo’s, and it seems that their underboss would like to meet with me to discuss it,” he said. Sans waited patiently. After a few moments he realized he was finished.

“er, and? are yous gonna go?” Sans asked, hoping it wasn’t a stupid question.

“Should I?”

This stunned Sans completely. He was the underboss, sure, but this was mainly because of his strength and brute force. Not to mention his habit of being able to wind up in places he shouldn’t be able to get into. He also stuck to the code of silence no matter what he was doing, even blackout drunk. He was clever, sure, but he was equally as lazy. He was not responsible for making plans, at least not big ones. And Gaster rarely, if ever, asked for his opinion.

“well… things seem to be goin really swell for us already, especially with what you’re buildin’.. but the Misers have always kept a good eye out for monsters, they even got a couple in their group. They’re the only group, ‘sides us of course, that helps watch out for monster’s hides in this town… but that don’t mean it’s not some sorta trap, right? or, or they could just be tryin to get a feel for yer magical capabilities by usin some of their monster recruits… w-what did they want in exchange? hell, what’s in it for anyone? what’s the proposition?” he realized he’d been rambling aloud, unsure what to make of this development. Gaster had done business with rival gangs before, all of which despised monsters and their very presence on the surface. The Misercordia’s were one of the older groups, and the Gasters were one of the newest. It could be possible that the influx in mobs had the Misers wanting to take them down a peg. Still, it wouldn’t make any sense for it to be them. And Sans wondered briefly why they had never done business before.

“They’ve been doing some spring cleaning, and they’ve gotten word on rival outfit activity. However, it wasn’t concerning them,” he said darkly.

“oh?” was all Sans could say.

“They’re willing to exchange information on a plan to sabotage us in exchange for a very small amount of territory by the river. This is a sector of abandoned buildings that we don’t use. The original plans were to fix them up, if you can recall, but the placement and the water damage made it not worth the effort at the time. I’ve been debating about what to do with that sector. It’s quite small, but any loss of territory is… an unwelcome outcome,” Gaster sat back in his chair and elected to relight his cigar. After striking the match against his teeth, he toasted the end lightly before taking a drag.

“Of course,” he continued, “The information they have may be less significant than they claim. But I’m nothing if not fair. I think an attack on our people is worth four sodden buildings, don’t you?”

Sans nodded quickly. “sooo.. if they tell you what’s up, and they’re right about what’s up, they get sector..” he thought hard for a moment, really trying. “twelve?” Gaster nodded his approval. “and if not, and you don’t give them the territory, then what?”

Gaster stopped smoking long enough to give Sans a look that was bone chilling. There were no lights in his eyes, and the way his head tilted to the side like a doll reminded Sans of something lifeless and nightmarish. Green smoked seeped out from the fine cracks in his skull, and the light creak of his bones could be heard in the deafening silence.

“If they dared tell me lies, the Gasters and the Misericordias would no longer be on friendly terms.”

**Notes for the Chapter:**

> The plot, she thickens


	3. Big Cats

**Notes for the Chapter:**

> my guys I have so many chapters of this story written it's not even funny. I keep trying to not post them and save them for a rainy day but patience is not in my nature. I hope y'all like it. Also, this is the last shorter chapter before they start to get longer, the next few I've written have 2x the word count so cheers bro I'll drink to that
> 
> \- before we go any further, there will be frans and frans smut in *way* future chapters, but this is more of a slow burn/angsty typa shit just so we clear

Sans and Papyrus ate in silence. Too busy thinking about his uncle’s departing words, he barely registered when his fork scraped the plate, or when Papyrus took it out from in front of him.

_When are we leaving?_

_They’ve made a request. I am supposed to arrive… alone._

Sans couldn’t believe the balls on these people. Not only requesting territory for some word of mouth, but asking the Don to come _alone?_ There had to be more to this thing than what Gaster was letting on. Either that or the attack was really, really serious. He knew his uncle’s magic was powerful, and he was capable of taking on a small group of humans by himself. But these weren’t normal circumstances. The deck was in their hands, and whether Gaster liked it or not, he was just a card at the moment. Sans didn’t like it one bit. He pulled out a cigar of his own and made himself comfortable in the chair.

_This is gonna be a long night._

* * *

 

After Frisk’s shift at the bookstore she milled about, looking for a new subject she could delve into. An avid reader, she made it her personal goal to have some common knowledge on all subjects. A well educated person can be awfully dangerous. She considered information important currency nowadays, especially with all of the gangs plaguing the streets. She couldn’t help her mind from roaming to Sans, with his deep, earthy voice. She didn’t know a skeleton, something made of bones, could be so large and overwhelming. Her cheeks heated up. She wondered if he really expected her to call.

 _He’s got cards with his phone number on em, Frisk! I wonder how many ladies get one per day. Would he even know it was you callin?_ She asked herself. What if he does? _I get the feelin I don’t want to find out._

After plucking up and checking out a book on edible plants, she waved goodbye to her boss and stepped out the door. To help busy herself throughout the day, she’d made a beautiful display in the front window with paper origami. This week’s subject was “Cooking on a Budget.” Not very interesting, but she made it eye catching. Skipping off down the street with her book poking out of her bag, she caught a glimpse of herself in the shop windows. She used to cut her hair short, but had begun growing it out as a young teenager. If she cut it her and Chara looked almost identical, which is something that bothered her. He was a few heads taller than her now, and she cursed her short stature for the umpteenth time in her life. Chara was beautiful, especially with his dainty nose and sharp jawline, but Frisk wanted to be unique. So even when all the ladies in town began chopping their hair off to keep up with the latest fashion, Frisk’s waist-length hair remained. She got a lot of mixed looks for it. Sometimes there would be wolf whistles, and sometimes she would get a “cut your damn hair, lady,” but she never complained unless someone tried to touch it. Then there was a problem. Frisk never minded making a scene. She wore it loose during the day, but always made sure to braid it and tuck it up at night. You could never be too careful walking these streets, and she had thought about bringing a gun to work more than once. Always deciding against it, she remained convinced that she could handle herself. Frisk had bumped into trouble more than once, sure, but she always managed to walk away.

She couldn’t wait to get home and tell her brother about her day. After looking at the pretty gold lettering on the business card (like she had been doing on and off all day), she tore the thing to pieces and sprinkled them in a nearby garbage can. If she was unwise enough to call Sans up, she had the number memorized.

 _Such a shame,_ she thought. _It was a real pretty card._

* * *

 

 _­­What the hell are the bosses thinking?_ Gerson wondered, his apprehension shown plain on his face. _I understand making business deals, but inviting him_ here? _It makes no sense!_

Alice nodded in agreement, as if she were able to read the old turtle’s thoughts.

“I suggested to the boss it would be better for everyone if they just met up in some joint, but you know he doesn’t listen,” she said good naturedly.

“What does the Don say?”

“He’s out for the day, but you know the whole thing had to be his idea. Nothing goes on here without his say.”

“That’s not true, I heard they let their brother call the shots when they’re not here.”

“Then your hearing is going, old man,” Alice teased. “It doesn’t matter if they’re blood, The older brother’s got him strapped. He may be the underboss but he’s always executing direct orders.”

“What do you know? You’re new.”

The pair of soldiers fell hushed as a black limousine rounded the corner through the thicket of trees. Gerson adjusted his worn, tan hat and squinted his good eye. His only eye, really. After a scrap with some White Snakes a few years ago, his right eye had been popped out like a paddle ball. It didn’t matter, though. He didn’t need two eyes to strangle the both of them-just his hands.

Barely outside of city limits, one of the Misericordia’s bases stood tall and proud, with sharp iron gates encircling the property. It housed some of the older members and the untrained individuals, ones that were too trigger happy and stupid to be released into the city just yet. The others had done their time in the harshness, and didn’t have body parts like they used to. It was a tough business. Thankfully, the Misericordias didn’t consider someone no longer useful because they had a bum leg or some missing fingers. They were all well taken care of here, and if you followed the rules you were treated like family. The acceptance process was grueling and full of many trials that most of the recruits weren’t even aware of. More and more spies were being weeded out every year, but none were clever enough to infiltrate any of the four bases yet. Those that were serious about joining had to be put on sentry duty first with a babysitter (which they were unaware of), then pass a lie detecting test (also unaware of), then they were put on cleaning duty to see how they mingled with the rest of the group, then they had their SOUL examined, then they were extensively trained, and then it was time for their first orders, which would be closely monitored by an elite team.

 Gerson may have been old and a little bit maimed, but he was neither considered incapable or ‘retired’. He joined the Miser’s almost immediately when he came out of the Underground. You wouldn’t have guessed it because of his placement, but he was one of the few that had seen the Don in person. He smiled to himself fondly. This was a fact he kept to himself. Faking powerlessness allowed him to get in good with any new recruits that believed he was some daft old turtle that was too simple to move up in the ranks. No, Gerson was skilled at what he did. Deciding what was good to keep and what was trash to take out was an important job. Even if he only got the credit in secret. He hadn’t decided about Alice just yet. He’d let that little comment slide, but nothing got passed him. He always made his weekly reports to the Don very detailed.

She was a small girl, but she was muscular. The organization had been letting women in more frequently, but mostly just monster women. Some gangs in the city thought this was laughable. They were never left laughing for long. The ladies of the group seemed to work harder than anyone else in fear of losing their opportunity, so everyone remained in tip top shape. Alice was no exception, but she had a mouth on her. Not for cussing; for complaining. The turtle monster was willing to give her a fair shot. She had the potential to be a sweet kid. They had allowed her in because of her phenomenal gun slinging skills and her sticky fingers. During the monthly rugby tournament she had even passed the ball to him. Still, none of this made up for the fact that she always critiqued the way Gerson did his job, and he didn’t doubt she would do that to her higher ups as well. He was _not_ going to get blamed for that. Some straightening out may be in order.

As Don Gaster’s limo neared the gates, Gerson and Alice turned the key in the large padlock and pulled the iron doors back. With a little elbow grease and the harsh rattling of chains, the limo cleared the first entryway and the gate was shut and secured again.

“I wonder what the meeting’s about,” Alice said. After a few moments silence she added, “I can’t wait to get out in the city and do some real work.”

“Be patient,” Gerson said softly. _You might not make it that far._

* * *

 

“Don Gaster! Such a pleasure to finally make your acquaintance!”

Gaster was torn from his reverie, imagining how wonderful the mantlepiece would look in his office. It almost appeared to be sculpted out of bone, each intricate detail having to be carved with great skill. The design looked like hands trying to push out of the work itself, being thinly veiled by a gossamer sheet. A masterpiece. He was always one to appreciate work that required you to be hands on. If he were Sans he may have been tempted to think up a pun out of that.

“Hello,” he croaked. “You must be Mr. Misericordia.”

“Ah, isn’t it a mouthful? Just Miser is fine by me, Don Gaster. I truly appreciate your promptness. Isn’t the décor lovely? We made that out of one of our fallen soldiers. Pure ivory. He was a good man,” Miser prattled. If that was a joke, Gaster wasn’t amused. He wasn’t sure he liked the underboss. Something about him left a bad taste in his mouth.

The young man was dressed in a powder blue linen summer suit with a cream undershirt. He had no expensive jewelry on. Actually, the only accessory he donned was a bright yellow buttercup poking out of his lapel. His hair was a light brown, almost golden at the tips, and it softly stuck out in multiple directions. His shoes were the same soft brown as his hair, but his eyes were a richer shade. He was clean shaven, and he had the appearance of someone that had never quite eaten their fill. How could this lanky mobster instill such fear in his rivals? Gaster wondered if most of the tales about him were false.

After the two men shook hands (Miser’s was completely engulfed in Gaster’s, who stood at around 8 feet tall), they made their way down the ornately lit corridor. Peering up, he realized this was so because the ceiling was made of stained glass. The patterns were random, and it had no particular design. Just hundreds of shades of colors, all fractured together like an insane puzzle. They passed by a dozen closed doors, each with a different shaped door handle. When they made it to a large pair of double doors, Miser opened them with a flourish. The room was high ceilinged, but it was dimly lit. There was a large cherry oak desk with a kerosene lamp, a stack of papers, and a decanter full of an amber liquid. It sat on a metal serving tray with crystal glasses, and a box Gaster assumed to be filled with ice. The wallpaper was a deep maroon, adding to the shadowy appearance of the room. Behind the desk were large windows with the blackout curtains drawn.

“Please, have a seat. It’s important that you’re informed as soon as possible,” he said, a hint of sympathy in his voice. No, Gaster did not like this man at all. An aura of condescension followed him like fog. He wanted to take a peek at his SOUL to see what his LOVE was at, but he knew it wouldn’t make a difference. It was bound to be high, no matter what. He was an underboss after all. It really depended on _why_ he killed. That was something that took a bit more skill to determine. He decided he would do it once the conversation was over, as the process was a bit taxing and he needed his full attention directed to the problem at hand.

“Yes,” Gaster began, his voice a low murmur. “I really am curious to know how you so easily uncovered such a plot.” He kept any malice from lacing its way into his voice. It was imperative to play nice, especially in his current predicament. The thought of how easily he could crack every bone in Miser’s frail body like a small bird was at the forefront of his mind. Even if these humans pretended to tolerate monsters, it didn’t mean Gaster thought highly of them.

            If Miser was offended, he didn’t show it in the least. “Not me, Don Gaster! Don Misericordia was the one to stumble upon it. You see, that’s one of the main reasons they don’t show their face to the public. It’s much easier to snoop around when you look like the common folk, you see,” he explained, flashing a bright smile. “What really drew our attention were a pack of Smiley’s sneakin’ through our turf,” the smile fell, and Gaster thought he saw a spark of rage in his eyes. His otherwise crisp speech had slipped into an accent for a moment. The rage was gone as quickly as it had appeared. If Gaster hadn’t been paying awfully close attention, he wouldn’t have noticed it. The “Smiley’s” Miser was referring to were the North End Rotters, a group of vicious gangsters that were no strangers to murdering in public. They had no sophistication, no moral code, and most importantly, they had no problem with being insufferable rats. Whoever had the deepest pockets had their brief attention. Not an official part of any mob group, they did grunt work for anyone that paid them. Their prices were surprisingly cheap. When they had a paid hit, they were sure to carve a glistening grin that stretched from ear to ear. They really liked getting credit for their work, you see. The papers always had a field day with the Smiley Face Murders, the press in the city coming in a close second where insufferable rats were concerned.

             This answer did not completely satisfy Gaster, but he kept his teeth sealed. At least he hadn’t run into any trouble yet. If this was a setup or some type of ambush, it was blatantly obvious and in very poor taste. That didn’t mean he was going to let his guard down. For a moment he wondered where everyone was at. All he had seen so far were the sentries manning each gate and a guide that led him up the mansions stairs before returning to their post.

            “Anyhow, when we went to whack the lot, we overheard some suspicious dealings going on. You see, the boss doesn’t leave witnesses when they’re out alone. It’s either all or nothing. They were discussing a shipment of something I’ve never heard of before. And I’ve been on these streets since I was an even littler thing,” he smirked.

 _At least he knows it,_ Gaster thought.

“So we had to leave them all. It wouldn’t do to have survivors realizing we overheard their little playground banter. It could change the entire outcome. They are not very intelligent creatures, but it is better to be safe than sorry, don’t you think? We also have our good reputation to uphold. When we clean house, we don’t like to miss a spot,”

            “My apologies, I forgot to offer you a refreshment. I don’t suppose you’re fond of gin? We do have a full bar, if you’d like to pick your poison,” Miser said, taking a small pair of tongs and dropping ice cubes into one of the glasses. He poured himself a drink, and then added “Or if you’d prefer, we have some lovely kinds of Partagas?”

            Gaster was about to snap at him to get on with it, but a cigar did sound like it would hit the spot. He had just had one at home, but perhaps it would help him become less on edge with this entire situation. When a capo had reached out with the Don’s terms, he almost laughed and told them to walk away before he prevented them from ever walking again. Only the thought of a threat to his family is what prevented him from doing so.

_We have vital information. Some of you may be in danger. Arrive alone. You may bring a driver. No meeting in public. No weapons._

            Still, this had to be the most civil business meeting he had ever had. Usually he had to resist the urge to throttle humans in public. They had such a superiority complex, always snidely referring to him as “ _monster”._

_What are you? The city’s new pet?_

_You call yourself a Don? You barely have any members._

_Why don’t you crawl back into the hole you came from? And take all the other **monsters** with you!_

            No, just because this mob, this _human_ wasn’t doing any of those things, that didn’t mean Gaster had to like him. He wasn’t a starving dog that could be satisfied with scraps. The only thing that would tell if these people were trustworthy was time, and a lot of it. If they ever crossed him or lied to him, even once, he would put an end to their miserable existences, humans and monsters alike.

            “A cigar sounds lovely,” he said coolly, plucking a nutty brown torpedo from the box in Miser’s outstretched hand. It had a red band with gold foil, and the aroma of cedar and nutmeg wafted from the opened box. Miser offered him a wedge cutter, and soon both men were toasting their tobacco. Once Miser was satisfied, he drew in a breath of smoke and licked his lips.

            “I suppose it wouldn’t do to play the guessing game, so I’ll just come out with it: The Rotters were discussing a job that the Columbo’s had paid them to do. In return for the job, they would be paid well, but they wouldn’t be allowed to look inside of the shipment crates. The Columbo family didn’t want any connection to the heist, as it involves blowing up the North Ebott Bridge.” At this, Miser paused, looking into Gaster’s eyes directly. If he had any blood, it may have run cold. He could see where this was going.

            “I couldn’t figure out why they would commit such a _heinous_ crime,” he continued, “seeing as that is one bridge of three that connects our city to the rest of civilization. Why not blow up all three bridges? Unless, they needed the bridge that was going directly out of New Snowdin for something in particular. Then I thought to myself, 'who lives in New Snowdin?' Definitely not any members of a human mob.”

            “That is not possible,” Gaster said. He was holding his composure well, but on the inside he was flustered. _Months of planning, months of research, and someone leaked information about our shipment? Only a short list of people know anything about it. How?_  He straightened his back. Smoke curled out of his eye sockets. “The Columbos are murderers and petty thieves, they don’t have the resources to blow up something as large as the North Bridge, unless-”

Both men made eye contact, and they both spoke.

“They’re working with another mob.”

**Notes for the Chapter:**

> yeehaw  
> Just to let you guys know before s*** gets confusing, in this story there is going to be one 'organization' (*cough cough* a mob) five mobs, and three small gangs before we're all said and done. So basically eight groups in total. I know. Rough city. (it's more like a peninsula but who needs that - imma post a map to go with chapter 5 I think)   
> NYEH


	4. An Almost Alliance

**Notes for the Chapter:**

> Sans is a stalker and Frisk is keeping secrets

Sans had intended to stay up until his uncle got home, he really had. He thought about taking a few shots to ease his nerves, but he knew a few might turn into thirteen and he decided he didn’t want to sign his death warrant tonight. If the meeting went bad and Sans was drunk, his uncle would kill him. If the meeting went well and someone really was planning to attack the Gaster Mob, his uncle would kill him. There really was no scenario Sans could think of where he was going to be okay. To pass the time and try to make use of himself, he thought up plans for how to maximize the strength of his Gaster Blasters. While he did so, his eyes fixed on the grandfather clock’s pendulum and his vision began to blur. What did it matter if he took a quick catnap?

_The little minx was right, I am bone tired, heh heh._

He had been thinking of ways to improve his weapons for an entire five minutes when the woman’s adorable giggle replayed through his head. Was she flirting with him? Of course not. She just wanted a hotdog and he happened to have cleared the line for her. Still, he was sure he could convince her to want _his_ hot d-

Sans’ head fell back and he let out a light snore. As the exhaustion overtook him, he dreamt of the lady’s hair swishing against her backside as she led him down a dark corridor. Her hips swayed to and fro, luring him onwards. Occasionally she would throw a glance back to him, a knowing smile showing her beautiful white teeth. Her canines had been slightly more prominent than most, and she looked like a sexy little animal. Was that just in his dream or were they really like that? He willed them to be longer. Dream Lady complied.

_Ah, sleep. You never disappoint me…_

He tried to reach out and touch her, but his arms remained at his sides. If he couldn’t move his arms, he was just going to have to get closer. When he attempted to run, the world seemed to slow. It was then he realized they had never been moving forward at all, only trudging in place. When he forcibly tried to lift his feet, he heard her giggle again. This time when she turned to look at him her eyes were oozing black, her mouth a set of impossibly long, thin fangs.

He awoke with a start. Nearly letting out a yelp, he stared into Gaster’s dark eye sockets. His left shin ached. Gaster must have kicked him awake.

“Waiting up for me was quite unnecessary Sans, but I appreciate your unwavering vigilance,” he said with a roll of his eyes. “Go get some proper rest, we have a lot to cover tomorrow.”

“I’m awake now. How did it go?”

“I’m aware you’re awake, I’m the one that saw to that. I am headed to get some much needed sleep. You will be informed tomorrow, along with Papyrus. I don’t feel like constantly repeating myself.” His voice had taken on an edge, but he was not enraged. Sans couldn’t believe his good fortune. He looked at the clock: nearly three and a half hours had passed.

“yeah, of course. night,” Sans stifled a yawn in the crook of his elbow, and he stood. His bones let out a few creaks, and he shuffled up the stairs to his room. Pausing in the doorway, he strained to hear if his uncle was also going to sleep as he claimed. All that met him was silence.

* * *

 

This was shady. This was shady as fuck. Sans’ apprehension grew and grew until he decided to go for a walk to cool off. Conveniently, he ended up just outside of Grillby’s Bar. Who was he kidding, he needed a drink. The bell on the door gave a jingle as Sans entered, and the orange fire monster turned in his direction. Always looking spiffy, Grillby’s long sleeved white button-down and black vest were pristine. He straightened his already perfectly straight black bowtie: the cuffs of his shirt were crisp. Built almost like a human male, Grillby was able to fit into most human outfits because of his athletic build and slightly above average height. The only abnormalities were the seemingly lack of a mouth, a nose, his white hot eyes, and well, the fire. Most of the customers that knew Grillby were aware that he could form a mouth and speak, but it took some effort. His flames were a brilliant yellow towards the center of his body, and they darkened as they blossomed out. Upon seeing it was Sans, Grillby gave a knowing nod and went back to polishing a glass in his hand. The bar had several tables full of patrons that all seemed to be enjoying their meals. Even during the daytime, the place was a popular stop for former Underground residents. Grillby had rebuilt his bar to the exact same likeness as the one in old Snowdin, even going back to haul his favorite memorabilia like his signs, tables, and paintings. Some monsters had been talking animatedly, but when Sans entered the volume dropped a level. Being a frequent patron, customers tried to show respect to the skeleton mobster in the only way they knew how. There was a short chorus of “Hey Sans” from those that knew him personally, and they all went back to their previous conversations and meals.

Getting comfortable on a red barstool, Sans gave a nod to Grillby and said “hey buddy. I’ll take a small bottle if ya ain’t too busy overcleaning that glass.”

Grillby cocked an eyebrow at him but said nothing. Sans knew this because his glasses raised slightly on the right side, showing he was wary of how early in the morning it was for a drink.

“yeah yeah I know. ‘s why I asked for a small bottle. that’s how responsible I’ve become,” he said, puffing his chest out in mock pride. “eh, and here. for puttin’ up with me,” he smirked, sliding Grillby a stack of cash. “and for, yanno, the alcohol and mile long tab. see? me comin early in the day is a good thing, much less likely to forget my wallet at home. how’s it been Grillbz? how’s the wife?” Grillby gave a slow nod in reply and the corners of his eyes crinkled in what Sans had learned to be his version of a smile. Newly married, Grillby had bumped into another fire elemental upon reaching the surface a few years ago. Moving out of the Underground had allowed monsters to venture farther from their homes more safely, and some were even running into their soulmates. Grillby and Agni got married after a few short months together. Sans had joked that the sparks must’ve really flew, which earned him an indignant huff.

When Grillby went to pick up the stack, he dropped a few bills to the floor.

“what’s the matter Grillbz? losing your touch _?_ ”

The man did not entertain his joking with so much as a backwards glance. Grillby knew that would only spur him onward. It was best to get the drink in front of him before Sans let an entire array of puns fly back to back. Grillby would never admit it, but once in a while he enjoyed them, and he didn’t have the time to laugh today. Glasses to clean, you see. They couldn’t be spotty, not in his bar.

“aw c’mon Grillbz, I’m just _ribbing_ ya,” the skeleton said, leaning against the polished counter. A small red bottle, probably equivalent to around 10 ounces was placed in front of Sans. It had a red cap with a widened nozzle that slanted. Perfect for squeezing, he spurted it into his mouth absently. When Sans drank socially at monster establishments, he would get a thinned out version of ketchup in a cocktail glass. Human bars had 'bloody mary's', something that could be considered similar. The human’s version of ketchup was okay, but they always added too much salt. That crap was mass produced anyways. Any respectable monster handmade their ketchup. The Underground had been sealed away for so long that most monsters were still in the habit of doing things the old fashioned way, whereas humans had a shortcut for everything. Some older monsters complained about it, but Sans couldn’t deny that it was convenient.

“anyhow, there was something I needed to talk to ya about later, might as well get it outta the way now. this Thursday we’re gonna need the entire bar reserved. we have a meeting with some new… associates. it would be best if yer patrons didn’t see who it is, capisce?”

Grillby was no stranger to the Gasters arranging business meetings in his establishment. They were always courteous enough to inform him beforehand. Nobody else in the city got this type of special treatment, but Grillby had known Sans and Papyrus since they were children. However, they usually did it in a corner booth during normal hours of operation. This request made Grillby’s flames dim in question. Sans waved it off.

“see, it ain’t exactly monsters we’re meetin with,” he said unhelpfully. Sans had brought human business partners in before, but none that needed the bar empty. Those humans had been agitated, rude, and downright scared to be surrounded by so many monsters. Being outnumbered wasn’t exactly fun. Having no other monster witnesses in the bar bothered Grillby, but he didn’t voice his concerns. Wingdings Gaster was going to do whatever he pleased.

 _Whatever is best for monsters,_ he added, trying to steady his nerves. Grillby didn’t ask questions. He just cleaned his glasses.

By the time Sans had left the bar, it was nearly noon. He had thought about grabbing a bite to eat, but Grillby had already started to pyrograph a wooden sign with his finger containing the words “We Will be Closed Thursday at 9 PM”. Sans told himself that he didn’t want to bother him, but what he really wanted was to check out that hotdog stand. He doubted if the woman would go two days in a row, especially after seeing him, but he couldn’t stop himself. Plus, they were some damn good hotdogs.

 _I really wish I’d asked for her name_ , he thought.

After dipping into the alleyway behind the bar, he closed his eyes and envisioned the alleyway behind the cobbler shop in Ebott. It would take an obscene amount of his magic to go so far, but if he tried to walk across the bridge he might risk missing her. If he borrowed one of the cars, Gaster might ask him exactly what the fuck he thought he was doing. He grumbled at the thought of it. There was a ruby glow that emanated from his right eye socket while the other one became devoid of all light. The world disappeared around him in a wink, nothing but blackness as far as the eye could see. Sans knew that the time he spent here was almost nonexistent, but time slowed for him and he took a breath. Like nothing had happened, he was standing behind the shoe repair door, and he leaned against it heavily. Rich red smoke faded around him. Teleporting took the most of his magic, and it made him sleepy to boot. Sometimes he had wondered why combat was so easy and less draining for him, but Gaster had given a longwinded and complex explanation when he was younger that he barely understood, so he never brought it up again. There was a sign on the back door that said “Put your best foot forward and walk to the front, please”.

 _That's a good joke,_ he thought begrudgingly. _For some humans._

He lit up a cigarette while he gathered himself, and the match hissed as he tossed it in a suspicious looking puddle. His mind was a bit fuzzy and his tongue felt heavy in his mouth, but he told himself it was just from teleporting. If Gaster found out he was tipsy this early in the day, he would really be in for it. Speaking of Gaster, Sans needed to head home as soon as possible to tell him he reserved the bar. They were going to need to give Grillby a decent amount of compensation for being so accommodating. Sans knew that Grillby had been apprehensive, but he never questioned anything. He was a good guy.

Walking out of the narrow passage, Sans strolled through the park that contained screaming and laughing children. Whenever one would notice him they would stop their play to gawk. He thought about snapping at them with a “didn’t yer mommy ever teach ya that starin is impolite?” but he just kept walking. Sans had to admit that even for a monster he didn’t exactly look like the most approachable of fellas, but people could at least pretend. He wondered if that’s what his little kitten had done yesterday. The thought saddened him, but then he shook his head. Why did he think _his_ little kitten? He must have been more drained than he thought. Teleporting after drinking was never a good idea, but he had barely had anything. He bought some hotdogs after a brief wait. People didn’t clear out as much as yesterday, but most still parted and let him go through. Perhaps after seeing that he didn’t violently murder anyone in line before, they were more comfortable with keeping their spots. He could have made them move for their behavior yesterday, but he liked to consider himself a courteous customer. Besides, he had time to spare so he could wait for his little lady. _The_ little lady.

Finding his own empty bench under the shade of a tree, he chewed his hotdog thoughtfully after absolutely drenching it in ketchup. Then, in between bites, he would dip it in ketchup. It paled in comparison after having some of Grillby’s but he couldn’t complain. The hotdog was one of the best he’d ever had. He decided to stop by a monster French Fry vendor when he made his way back to New Snowdin to get his health back up. Drinking drained it slightly, and the huge dent to his magic didn’t really do him any favors either. While human food had more of a nutritional quality, it was only enough to fulfill hunger and stamina. Only monster food could boost his magic. After waiting around for a good twenty minutes and eating his three hotdogs as slowly as possible, he sighed in defeat. He wasn’t prepared for the wave of disappointment that came over him. He had given the girl his phone number to mostly see the reaction on her face, but now he was wishing she would call. Which she wouldn’t. He knew that. But still. He began to walk towards the North Bridge, unable to waste any more of Gaster’s time.

* * *

 

Frisk ducked back behind Woolworth’s and chewed her lip, deep in thought.

She liked to eat her lunch in the park because it was nearby and the scenery left her feeling calm after a shift of know-it-all customers. When she saw a familiar lumbering figure, she nearly choked on her biscuit. She didn’t have to go back to work today, she was only employed about four days a week and two of them were short morning shifts. Frisk’s family had been distrustful enough of the banking system to hide money all over the place, and when the Depression hit, they lost nothing. She didn’t need to work at all, really, but she met new people and she got all the books she could read. At first she felt guilty for taking a job from someone that might actually need it, but the ad stayed posted for more than a few days and she couldn’t help herself. It was the perfect opportunity. Watching Sans from under the cover of her cloche hat, she became painfully aware of how much longer her hair was than anyone else’s. She packed her lunch up slowly and ducked between a row of buildings. His back was to her the entire time, but she could tell it was him. He lumbered over behind a patch of trees where she could no longer make out his profile. That was the direction of the food vendors.

 _Whew, that was a close call,_ she thought. _Did he really like those hotdogs that much?_ This part of town was awfully close to the border between Ebott and New Snowdin, but it was still a long walk. She had researched Sans extensively since their encounter, and she wondered if he would have used his magic to come here. _Nah, he wouldn’t do that for a hotdog._ A part of her wasn’t convinced. She peered around, looking for the Gasters signature black limousines. They may have had other vehicles, but those were the only ones she would be able to recognize. There were none in her line of vision. After more than ten minutes passed, she decided to call it a day. There was no use in spying on him here. She would get no information she could use. It was time to go home. She began to walk to the west, in the direction of Ebott’s one lone mountain. Miles beyond it sat a sea channel, where more land could be made out faintly in the distance. This land was mainly uninhabited, so most people preferred to stay on the island unless it was to go off and game hunt. There had been an instance last year where some men had shot a large brown monster that they said resembled a caribou, and they insisted it was an accident. They got off with a slap on the wrist, and monsters everywhere were 'outraged' according to the media. More like terrified. Ever since then, most monsters preferred to stick to their villages in the intercity instead of branching out, much to the annoyance of the humans. Humans and monsters were mixed in throughout all of Ebott, but they lived in sectioned off groups and complexes. The only part of town where monsters and humans intermingled on a regular basis and inhabited the same buildings was at the base of the mountain, and tensions were still high. Even so, there were no “Monsters Only” or “Humans Only” signs. Whatever shaky alliance the townsfolk had there was working for the time being. Mob activity and crime was low in that area, and when the monsters had been released from their prison under the mountain, Frisk had observed it all. Many monsters moved as far away as possible, and a new Mob Group formed-The Gasters, run by the only three remaining skeleton monsters. They were powerful, and it didn’t take long before they seized territory from the Grimes Family. The Grimes were a mob of weaselly looking lowlifes, charging those in their territory unreasonable protection fees and providing their “special” services to any white human males that needed it. This mainly involved loansharking and smuggling anything into the city that one could possibly dream of. If anyone was unable to pay back the high interest rates, they were simply put down or inducted into the gang until they could pay off their debt. This included a brutal initiation where you could either take a beating that might kill you, or kill a member of a rival gang. This attempt also often resulted in death. Even if anyone ever managed to somehow pay off their debt (which was almost an impossible feat) most elected to stay in the Grimes Mob. It would have been considered rude after everything they had done to help some poor penniless soul, something that would also find you in the bottom of the Ebott River. For this reason, the Grimes had become the largest mob in the city. However, this certainly did not make them the strongest. Trying to put quantity over quality was rarely a good idea, and members of the Grimes dropped like flies all the time. They also had infiltrations and leaked information constantly. Now that the Gasters inhabited the land across the North Bridge where the winds blew coldest, the Grimes had been pushed into the bowels of the city. At first they moved as far South as possible after their defeat (which was the territory of the Cottonham’s), but once they grew in numbers again they gained confidence and spread out like the bubonic plague. Frisk shuddered in disgust. The city had always been like this, but she was going to work to put a stop to it, one way or another.

            She mounted the bus at the station closest to the mountain, and the driver gave her a knowing smile. He was the same old man that had been driving this route since she was small, and he used to give the young passengers suckers before they became too expensive. The bus was packed at this time of day, and Frisk elected to stand in case someone needed the last seat. Gripping the hanging strap, she surveyed the passengers before letting her mind drift off for the long ride. She recognized a few, and the others all seemed to have relaxed postures. They were all off in their own worlds, either reading the paper or staring transfixed out the windows. Frisk was satisfied with her assessment and allowed herself to do the same. Chara would be expecting her, but she always liked to use the payphone at the bottom of the mountain to catch up with him while she waited for a cab. If he had had any problems throughout the day he would have rang her at the bookstore, but she always asked anyways. His job was stressful most of the time, and Frisk hoped her small talk distracted him from the larger worries, if only briefly. Yes, Chara really was the best of them. She only hoped she could be as good of a person one day. One day. For the time being, she had work to do.

**Notes for the Chapter:**

> I know that buses like I'm describing weren't exactly a thing yet, but for some reason the bus scene felt necessary to me. I wanted to keep this mildly historically accurate, but it's a story about monsters in a fake town so I stopped caring about the minutiae. They had buses in the 1800's but not the standing, spacious public trash heaps we know and love. I guess I wanted to show that the mountain was more excluded from the rest of the city, and that monsters and humans could ride a bus together in that area or something? Anyways the cars and cabs are still supposed to be very *~20's~* so picture them like that for me, k thanks


	5. Pull Yourself Together!

**Notes for the Chapter:**

> We’ve got a boring lil chapter but do not fear ~ Frans-y shit is almost here

Sans was miserable. He didn’t know how and he didn’t know why, but nothing could be done to satiate his burning anxiety. When he was asleep he would have nightmares that he never seemed to remember, and when he was awake there were so many things to be done that he couldn’t get a moment of peace. Yesterday he had wanted to scope out the park again, but business at hand wouldn’t allow it. Tonight was the big meeting with the Misericordia’s at Grillby’s, and many security preparations were being made. Greater Dog was set to man the door while Lesser Dog and Dogamy were stationed on the inside. They all had colts strapped to their hips, and Grillby had a tommy gun hidden behind the bar. Gaster told Sans that Mr. Misericordia had no visible weapon on his person during their meeting, as well as no guards. This had most likely been a trick to instill a false sense of safety, and there was no way he was going to fall for it. Sans secretly thought he was being overdramatic. Papyrus refused a gun, calling them “uncivilized” and insisted his magic would suffice. Miser and his group were set to arrive at ten o’clock, and Gaster had made no special requests other than that the meeting be held in New Snowdin. The mobster readily agreed, even going so far as to ask how many men he could bring. The man was bizarre, but Gaster could begrudgingly admit that he had manners. While the rest of the administration was responsible for meeting preparations, Papyrus and Sans had an interrogation to get to.

“SAAAANS,” Papyrus whined. “WHY WON’T YOU PAY ATTENTION TO ME? I’M THE ONLY BROTHER YOU’RE GOING TO BE BLESSED WITH, YOU KNOW.”

“huh? oh, sorry bro. I’m just thinkin’ bout the meeting later,” he lied. After a fitful night of sleep, he had gone to pick up everyone’s suits at the cleaners before they opened to pass the time. Upon returning home, there was nothing he could do but pace the floor and try to gather his jumbled thoughts. Not long after, he and Paps had been given an assignment to pick up some humans that were creeping their way through a freight transport area at the crack of dawn. This was around the time when the one lone bodyguard was relieved and another took his place. The area was used to weigh goods before they would be carried into the city, and the Gasters paid the guards off to be informed of any unusual comings and goings at all times. Two unknown men were spotted sneaking through with trench coats, the collars flipped up all the way to the brim of their hats. They must have thought that the area was the prime shortcut instead of the main road to the bridge, but luckily the guard left his badge sitting at his post and had to double back for it. He said that they were last seen making their way back to Main Ebott City. Before the skeletons even had time to grab breakfast, they were being picked up by their driver and sped down the backroads. If these two were some type of spies, they were going to be in for a bad time.

“YOU SEEM DISTRACTED LATELY, IS SOMETHING ON YOUR MIND?”

“nah, nothin’ important. what’s it to ya, bonehead?” he grumbled.

“I WOULD NOT WANT MY DEAR BROTHER BEING A DUMBASS AND SCREWING ANYTHING UP. UNCLE WOULD NOT BE PLEASED,” Papyrus answered cheerily. Sans sighed.

“fair enough.”

The rest of the speedy ride consisted of the pair going over what questions they were going to ask and where they would split up if they couldn’t find the spies. It didn’t take long, however. Sans caught a glimpse of a suspiciously human looking leg disappearing behind a corner.

“Stop the car,” he growled. “d’ya see that?” Papyrus nodded resolutely, a sinister grin upon his face. “you take the left I take the right.”

Once Sans leapt from the car and grounded himself on the pavement, he teleported to the end of the alley they had disappeared down. Arms crossed, he heard the fast patter of two sets of footsteps and the splashing of puddles. When he heard them nearing the end, he swiveled around the corner and grinned.

“goin’ somewhere?”

The mystery men skidded to a halt, one of their hats flying off their head. Frozen like deer in headlights, they shared a look and spun on their heels to take off in the opposite direction. Papyrus rounded the other corner, softly smacking a long bone in one of his fists. They were trapped.

“Look fellas, we don’t want any trouble,” one of them said slowly, his beady eyes moving nervously from one end of the alley to the other. Sans watched carefully as he nudged the other man with his elbow. They stood back to back now, each one facing their skeletal opponent.

“oh yeah? then why’d you come lookin’ for it?”

In unison, they reached to their hips and whipped out dual pistols, but not fast enough. Sans swiped his challenger’s guns to the wall with a bored flick of his wrist. Papyrus elected to lift his man in midair, his deep purple magic encircling him. He began to choke, the lack of oxygen threatening to crush his lungs. He was then hurled onto the pavement, his guns clattering in two different directions. The guns then slid towards Papyrus in a channel of magic, where he gingerly scooped them up and placed them in the waistband of his black pants. Arms crossed, he narrowed his eye sockets.

“PITIFUL HUMAN! MY BROTHER AND I SHALL TEACH YOU A FEW LESSONS IN RESPECT. THIS IS SIMPLY NO WAY TO TREAT THOSE THAT ARE BETTER THAN YOU.”

Sans chuckled. His bro sure had a way with words. He walked over and grabbed the other guns that were held against a brick building. He had partly been hoping that the man would make an attempt to snatch them, but he remained frozen in place, his skin turning a sickly white.

“alright Paps, you got ‘em. we need to have our fun elsewhere before somebody sees.”

“BUT OF COURSE, BROTHER! NYEH HEH HEH, WHY DO YOU THINK I BROUGHT THIS?”

Before Sans’ opponent could turn to see what he was talking about, a bone was brought down on the back of his skull.

* * *

 

“look who decided to finally grace us with his consciousness,” a low voice said. All he could do was groan in reply. “hey pal, I don’t have all day.” There was an audible sigh. It was nice with his eyes closed. Nice and dark. There was a throbbing in his head, and he was sure if any light went into his eyes his brain would beg for mercy. So he kept them closed. “alright, but don’t say I didn’t warn ya. let ‘er rip, Paps.”

“NNNNGAHHHHHH!!!”

What would have been a deafening scream was muffled by a large gag stuffed into the gangsters mouth. His vision blurred and pain ignited every vein he possessed: he was glued in place. He couldn’t have moved if he tried. There was some invisible force locking his joints and numbing his mind. His jaw was clenched so tightly he thought he might break his teeth. The experience was sickening. Something was really _really_ wrong. Fear coursed through his body and he tried to look around the room. There were clamps on his bare feet and clamps on thick wires that tied his arms to his torso. The wires led to a machine. The terrifying skeleton with the black suit and red scarf had his hand on the switch, a smug smile on his face. He was taller than the other one and thinner too. Instead of having a round grin full of sharp teeth, this one had a jagged mouth that stretched all the way to his eye sockets. He couldn’t tell where the empty black holes in his face were looking, but he was pretty sure they were at him. The monstrous skeleton that stood around a foot shorter was kneeling next to the man’s face, and one of his eyes glowed red. The other was black as pitch. He had a blood colored bowler hat on his head with an even darker band around it. The man could have sworn he smelled the scent of decay leaking out of him.

“now listen buddy. We don’t wanna hurt ya unless we have to, understand? We just have a couple questions ‘s all,” the skeleton gave him what may have been intended to be an encouraging smile. He started to shake. The cloth was roughly yanked out of his mouth.

“Y-yeah, anything, t-t-tell me what you want to know,” he gasped, the pain still threatening to make him black out. He knew he couldn’t believe him, but he didn’t want to die. The threat of death so close made his heart pound, all of his reflexes telling him to run. But he couldn’t. Across the room, his partner eyed him warily. There was a gag in his mouth as well and ropes covered him from midsection to toe, but he had no electric torture device strapped to him. He hadn’t been in the gang long, but he knew all that was important was sticking to the job you’re on until it becomes no longer worth it. He decided this was no longer worth it.

“see, John over there told us everything already, and we just wanted to make sure we have the story straight. not so hard, right?” the skeleton gave him a sympathetic pat on the shoulder. “we want to know if this is all one big misunderstanding. because my brother over there, Papyrus – say hello Papyrus,” the skeleton that must be named Papyrus gave an enthusiastic wave, “he told _me_ that you guys were trying to shoot us, and I said ‘no Paps, they were just having a bit of fun. Of course they would never shoot us,’ and so we took this bet, you see. since I was right about you guys not shooting us, because you would have tried _much_ harder than that little display if you were, he told me we might be able to find out some stuff. we bet which one of our guys had the most valuable information. we decided whoever did was the one we were gonna let go and the other one… well, we were gonna decide that later.” The shorter skeleton stood, walking over to a cheap folding chair that sat in the center of the room. He removed his hat and scratched the back of his skull, the clawed fingers making a dull scraping sound. “but of course, if you don’t know nothin’ I guess Papyrus would win, and I hate to lose. You don’t want me to look stupid, now do you, uhhhh?” the skeleton gave him a pointed look. It took painfully long to register.

“S-steve.”

“right, right, _Steve._ So, Steve, this is your time to shine.” He waggled his fingers. “dazzle us.”

Over the next ten minutes Steve spewed out every thing he had learned since joining the North End Rotters. He would have told them about everything he got in trouble for in grade school as well if Papyrus hadn’t held up his hand.

“SANS, THIS HUMAN IS ANNOYING. I THINK MINE IS BETTER,” he said. The skeleton named Sans looked hurt.

“yeah, he’s a little soft in the head, but he’s just warming up. why doesn’t the Great and Terrible Papyrus grill him for a minute? you know I’m not good at this stuff. people tend to talk more when the person asking them has good looks, too.” Papyrus looked flattered.

Steve stiffened. Grill him? Oh no, no, please god no, he wasn’t sure he could handle another zap of electricity from that terrible machine, _no!_ Breaking out into a cold sweat, he squeezed his eyes shut and braced for the worst.

“SANS, I THINK HE IS BROKEN,” Papyrus said, shuffling closer to the trembling man.

“nah, he’s just in _shock_ I think, hehe. C’mon Steve, you’re embarrassing me.”

“HMPH. WELL I HAVE SOME QUESTIONS, SO LOOK AT ME WHEN I AM SPEAKING TO YOU.”

Steve reluctantly cracked one eye open and realized that he was only going to be interrogated, not tortured. He opened his other eye and nodded vigorously.

“WHAT WERE YOU DOING IN NEW SNOWDIN?”

“We were here to see how long it took to get from the shipment area to the bridge on foot,” he hesitated. If these skeletons didn’t kill him and he let any more information slip, the Columbo’s would.

“ANNNNND?” Papyrus prompted, visibly annoyed. Sans interrupted.

“listen kiddo, before you go any further I think it’d be in your best interest to let you know we already cancelled our top secret super awesome shipment. we know yer workin’ for the Columbo’s too, and not just from Johnny boy over here. found that shit out ages ago. what we want is stuff we might _not_ know, as in something of _value._ If you can’t give us that, well, we’re gonna have to charge you as today’s loser,” this statement was accompanied with a wink. Papyrus gritted his teeth, visibly irritated. About to make his way back to the machine, Steve got ahold of his senses.

“W-wait! I have something!”

“GOOD. I SHALL HAVE YOU KNOW THAT MY PATIENCE IS ALMOST UP.”

“Yeah, um, uh, the Columbo’s, t-they had enough money for all the stuff, you see, but not a way to get it! Their connections outside of the city weren’t willing to send in that much dynamite, said it was too risky,” he licked his lips, nervously glancing between the skeletons to see if any of this was going to save his skin. “S-so they hired some expert smugglers! The only group I know that could do a job that big is the Delacruz mob! I’m not c-certain but it has to be them! It has to!” he was becoming frantic now, desperately racking his brain for any whispered conversations he may have heard. One of them flitted through his brain and he kept talking before it slipped away. “N-no, wait, I did hear something, yeah, yeah I did. They s-s-said s-something about the s-sun finally rising in the east, lots of activity, u-um, uh--” Sans held up his hand to stop him.

 _Makes sense,_ Sans thought. The Grimes family had been the initial suspects because they were still all bent out of shape over their loss of the North, but they lacked the organization necessary to do big jobs. Not to mention they no longer had a secure base that anyone was aware of. They were a mob without funds or a strong leader. This was what led to their undoing in the first place, and now they had no territory as well. The Delacruz, on the other hand, were a bunch of racist bastards that could get anything into the city through the East bridge where their land was located. A small gang known as the White Snakes operated on the south edge of the Delacruz territory. They were a group of white supremacists that lynched and incinerated in grotesque delirium. The Columbo’s had a small bout of territory in the heart of the city, almost engulfed by the Misericordia’s wrapping around them. To go anywhere, the Columbo’s needed to go to the East Bridge or the northwest passage. Most people were permitted to travel through New Snowdin, but ever since the Gaster’s power had grown, rival gangs were wary. However, they usually didn’t venture far because the heart of the city contained almost anything any person would ever need. It may have been a small territory, but it was decidedly valuable. The Misericordia area snaked up to the mouth of the North bridge and all the way to the West, including Mount Ebott and most of the waterfront. They had the largest expanse of land, but the amount of people thinned out the farther West you headed. That left the Cottonham Mob in the South, the city’s main source of black market goods and liquor production. The Cottonhams had befriended the Grimes when they fled South, and in turn had a business agreement where the Grimes would smuggle alcohol and racketeer all around the city. Sans could see how and why the Delacruz mob agreed to help the Columbo’s. This would be useful to his uncle.

“dunno about you Paps, but I’m starving. practically wasting away,” Sans commented offhandedly. “wanna grab some lunch?”

“INDEED! I WOULD SAY WE HAD A MOST PRODUCTIVE MORNING. WE DESERVE IT,” Papyrus said, one hand on his hip and one raised in the air. His scarf fluttered behind him in a nonexistent breeze. As they shuffled towards the exit, he seemed to remember something. “OH SANS, WHAT ABOUT THE HUMANS?”

“right! right, duh,” Sans audibly smacked his forehead. “I’ll untie this guy and you untie that guy, yeah?”

Papyrus nodded. Once both men were freed and helped to their stiffened legs, they looked up at the monsters. Before either one could speak, Papyrus and Sans drew each man’s gun on the other and shot them once in the chest.

* * *

 

Shoveling nice cream into his face, Sans spoke around his plastic spoon. “what do ya think Paps? Did we _jump the gun_?” melted chocolate leaked from the corner of his mouth.

“DON’T TALK WITH YOUR MOUTH FULL SANS, IT’S REVOLTING.”

Sans rolled his eyes and kept eating. “I THINK UNCLE WILL BE MOST PLEASED. THE SHOOTOUT WAS A NICE TOUCH.”

 _Aw, was that a compliment?_ Sans thought. After clipping the two men, Sans had teleported John to a dank alley in an area that he knew the Rotters operated in regularly. He placed him with a gun in his hand and his extra in his pants holster. After making sure both men used the same bullets, a silencer was screwed onto Steve’s gun. Sans crouched to a shorter height and fired a shot at the building before blinking back to Papyrus’s side. He hadn’t wanted the amount of bullets in John’s chamber to not match up or have the time of the shots warrant any suspicion. The original plan had been to put both men across from each other, but Steve had electrical burns all over his feet. They elected to take him back home and toss him against their fence, watching his body plunk down the hidden doors. Both brothers listened to the sickening _thump_ as the body hit the bottom with a sound like a pumpkin bursting open. After that, they decided to get some nice cream.

“where’s he at anyway? seemed like he was in a hurry this mornin’.”

“OH, DOES IT MATTER? NOW YOU CAN TELL ME WHERE YOU DISAPPEARED TO THE OTHER DAY FOR ALMOST AN HOUR,” Papyrus said. Sans glared at him.

“since yer bein’ so nosy, I’ll have you know I went to get a bite to eat,” he snapped.

“NOT AT GRILLBY’S? I DIDN’T KNOW YOU ATE ANYWHERE ELSE.”

To Sans it sounded like Papyrus wasn’t going to let it go.

“when Uncle G. sent me out for parts a few days ago I found a new little place,” he said easily. This satisfied Papyrus.

“AH, YOU WILL HAVE TO SHOW IT TO ME SOON,” he said, focusing on his frozen treat. Sans outwardly shrugged, but inside he couldn’t help but overthink. If he ran into the dame again she might try and talk to him, or if he didn’t approach her first she might think he was ignoring her, or if she saw him again and he couldn’t talk to her because of Papyrus she might realize he was going there to talk to her and then she might never go there again, or- Sans stopped himself. Why was he complicating things so much? The anxious feelings that had been plaguing him the last few days were back, and he couldn’t help but wonder what was wrong with him. This was strange, wasn’t it? Thinking about a person this much? And why did it freak him out?

After getting back home, Papyrus got busy in the kitchen and Sans took off his dark brown jacket. They had all day before the stupid meeting, and he was determined to at least get a little sleep before then. He sat and kicked his feet up on the coffee table, one thumb hooked around his suspenders. He undid the top two buttons of the dark red dress shirt he was wearing, and he placed his hat beside him. At least Paps was making lunch and not dinner. He wasn’t a bad cook really, it was the lack of variety that did him in. Sans didn’t mind the sandwiches and snacks for lunch, but some type of spaghetti for dinner _every single night_ was depressing his taste buds. The stuff had tasted like watery garbage noodles at first, but his brothers skills were improving. Very, very slowly.

After eating lunch, Sans thanked him and helped dry the dishes before going up to his room. He only planned to get a couple hours in, but he awoke to Paps shaking his shoulder. The sun must have been low in the sky, because dim rays painted his bedroom floor through the blinds.

“wha time’s it?” he asked groggily.

“AROUND EIGHT-THIRTY. I THOUGHT YOU MIGHT WANT SOME DINNER BEFORE THE MEETING.”

Before Sans could wrap his mind around having to consume more pasta, Papyrus added “UNCLE SAID WE SHOULD JUST EAT AT GRILLBY’S TONIGHT.”

 _Well, I can’t say he never did anything for me,_ Sans thought with relief. It would be smart to get a magical pick me up for the crew in case things went to shit.

“aight, I’ll be ready in a jiffy” he said with a sigh. Meeting the Misericordia’s didn’t really help spike his appetite, but how could he say no to a burger at Grillby’s? He dressed swiftly, his temples throbbing. Why did tonight have to be one of his bad moments? Fatigue overtook him. He felt like he could sleep for so much longer. Bones complaining with every step, he crept down the stairs to a potentially deadly dinner date.

* * *

 

As Grillby cleared their plates away, Sans looked at the clock. It wouldn’t be long before the Miser’s Underboss arrived.

Upon their arrival, the other customers had all but dispersed already. When those who remained saw the approaching Gasters and made the connection with the sign, they ended their meals early and left cash up on the counter with several hurried ‘keep the change’ comments. Grillby gave a disapproving look. It clearly read _you’re early._ He immediately began pouring drinks.

“for someone made-a fire you’re pretty fluid at that,” Sans commented. Papyrus made an indignant sound.

“no need to flare Grillbz, I’ll have you crackling in no time,” he continued. Gaster hissed.

“ _Enough._ Get your food so you aren’t entirely useless if it comes down to a fight.”

“alright, alright. thought my jokes were on fire, but you can’t blame a guy for frying. I’ll take my usual, buddy,” Sans winked.

“AND I WILL HAVE YOUR FINEST SPAGHETTI WITH MEATBALLS, MR. GRILLBY,” Papyrus said with a flourish, snapping his menu closed as if he had actually been deciding. Gaster ordered a sandwich before going to a back corner to discuss something with Lesser Dog. Now it had been thirty minutes and they had time to spare before the rival mob arrived. Sans elected to hang out with Grillby in the back, already having been over the plan with his uncle a dozen times. He shot Grillby a few more puns before being shooed out, and now he and Gaster were talking in hushed tones around a booth. The hour was drawing near. Sans remembered all of the horrible stories about the Misericordia’s Underboss. He was a ruthless killer, never sparing anyone in his wake, often leaving a trail of bodies. They would cut throats, stab important human organs, and often large groups of people would go missing at a time. The thought of coming face to face with someone so legendary on the surface didn’t’ exactly make him nervous… but it would be wrong to say he wasn’t skeptical about all of this. He had met members of other mobs before, even a capo or two, but this felt different. The Miser’s were the big guys. The elusive mountain people. The only other mob that had monsters of their own. There was barely any information floating around the streets on them, and believe him, he had checked. Now all there was to do was wait and see this ruthless crime lord for himself.

Lights flashed through the windows, signaling an incoming car. Papyrus was sitting at the bar, facing the door expectantly. The vehicle parked in the back as instructed.

 _here we go,_ Sans thought, already checking his stats. _showtime._

Greater Dog opened the doors, and a man walked inside. He was tall, for a human, an entire foot shorter than Sans himself. However, he was awfully thin. Not unhealthily so, just to the point where it was apparent that not a lot or muscle or fat occupied his small frame. Dressed in a navy suit with a dark undershirt and a blinding white tie, he had an overall boyish appearance. He grinned cheekily.

“Mr. Miser,” Gaster began, rising to greet him. “You’re early.”

Sans briefly wondered why his uncle was already exuding such a sour mood. It may not be apparent to a human that has little knowledge on soul reading, but Sans could already tell that ‘Mr. Miser’ rubbed Gaster the wrong way. As Sans suspected, his uncle's behaviour didn't perturb the man in the slightest.

“My apologies Don Gaster, but I always prefer to be early rather than late. I could step outside for the next seven minutes if you are unprepared,” he said, his tone light and chipper. Sans winced.

“No, by all means,” Gaster replied. “I would like to introduce you to my nephews, Sans and Papyrus.”

They all exchanged pleasantries before settling down at a table. Miser complimented the entire setting: the atmosphere, the decorations, the lighting. Sans knew he should be annoyed, but he was becoming cautiously more relaxed. After the initial shock of seeing the man, he had immediately warmed up to him. They had nothing to worry about with this puny human, and he hadn’t even brought anyone with him. Miser was seated between Sans and Papyrus, both looming over him. Papyrus stayed silent for the majority of it, shooting daggers with his eyes. They discussed logistics, weaponry, and locations for future meetings. There was a lot of ground to cover. As it began to bleed into the early hours of the morning, Gaster motioned Grillby for a round of drinks that helped boost stamina. He placed the shot glasses down on the table, full of a shimmering turquoise liquid. When the light hit them right they were a pale blue. Miser hummed appreciatively. Sans had tried the drink before. It tasted like a mix of cucumber and water, but soon after the effects would take place. Any soreness around the eyes would dissipate, as well as stiffness to the limbs.

“HUMAN,” Papyrus began, before the conversation took off. “YOU DO NOT SEEM SURPRISED BY THESE MAGICAL HEALING EFFECTS. WHY IS THAT?”

Truthfully, Sans had been wondering the same. After commenting on almost everything in the establishment, Miser seemed least enamored with the drink. This is what most humans would appreciate, some even asking how it works.

“Oh!” Miser said. “I’ve familiarized myself with many types of magic. Always best to stay well-informed. I noticed that this is mostly green magic with a hint of blue. Perfect for a refreshment. Truly delicious. My compliments to the chef.”

This answer satiated Papyrus, and he began to eye the human with more interest and less hostility. The group continued on with a renewed vigor.


End file.
